Araglaucine C - Compound Card

Araglaucine C

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Araglaucine C

Structure
Zoomed Structure
  • Family: Plantae - Papaveraceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Isoquinoline Alkaloid
Canonical Smiles COC1CC(c2c1c(C(=O)OC)c(cc2)C(=O)c1nccc2c1cc1OCOc1c2)OC
InChI InChI=1S/C24H21NO7/c1-28-16-10-19(29-2)20-13(16)4-5-14(21(20)24(27)30-3)23(26)22-15-9-18-17(31-11-32-18)8-12(15)6-7-25-22/h4-9,16,19H,10-11H2,1-3H3
InChIKey DSLGGHYYYHBEBV-UHFFFAOYSA-N
Formula C24H21NO7
HBA 8
HBD 0
MW 435.43
Rotatable Bonds 5
TPSA 93.18
LogP 3.76
Number Rings 5
Number Aromatic Rings 3
Heavy Atom Count 32
Formal Charge 0
Fraction CSP3 0.29
Exact Mass 435.13
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Glaucium arabicum Papaveraceae Plantae 2072396

Showing of synonyms

  • Elbermawi A, Sallam A, et al. (2018). Bioactive isoquinoline alkaloids from Glaucium arabicum. Phytochemistry Letters, 2018, 28, 139-144. [View]

No compound-protein relationship available.

Structure

SMILES: C1CCc(c12)ccc(c2)C(=O)c(ncc3)c(c4)c3cc(c45)OCO5

Level: 1

Mol. Weight: 435.43 g/mol

Structure

SMILES: O1COc(c12)cc3c(c2)ccnc3

Level: 0

Mol. Weight: 435.43 g/mol

Structure

SMILES: C1CCc(c12)cccc2

Level: 0

Mol. Weight: 435.43 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.7
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.560
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.84

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.070
Plasma Protein Binding
59.19
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Inhibitor
CYP 1A2 Inhibitor
Inhibitor
CYP 1A2 Substrate
Substrate
CYP 2C19 Inhibitor
Non-Inhibitor
CYP 2C19 Substrate
Non-Substrate
CYP 2C9 Inhibitor
Non-Inhibitor
CYP 2C9 Substrate
Non-Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
4.470
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.050
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.270
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.800
Micronucleos
Toxic
NR-AhR
Toxic
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Safe
NR-PPAR-gamma
Safe
NR-TR
Toxic
T. Pyriformis
-191.670
Rat (Acute)
3.440
Rat (Chronic Oral)
2.440
Fathead Minnow
6.010
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Toxic

General Properties

Boiling Point
492.210
Hydration Free Energy
-2.940
Log(D) at pH=7.4
3.820
Log(P)
3.03
Log S
-4.65
Log(Vapor Pressure)
-8.72
Melting Point
154.16
pKa Acid
8.75
pKa Basic
1.81
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.9497
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.9418
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.9308
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9263
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.9207
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.8880
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 3 0.8649
NADH:flavin oxidoreductase Sye1 Q8EEC8 Q8EEC8_SHEON Shewanella oneidensis 3 0.8615
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 4 0.8499
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.8430
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8411
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8406
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8397
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8324
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8324
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8176
Methionine aminopeptidase 2 P50579 MAP2_HUMAN Homo sapiens 3 0.8081
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.8034
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7973
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7931
Multidrug-efflux transporter 1 regulator P39075 BMRR_BACSU Bacillus subtilis 3 0.7924
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7867
Serine/threonine-protein kinase PLK2 Q9NYY3 PLK2_HUMAN Homo sapiens 3 0.7839
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7830
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.7817
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7809
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7788
Ferric enterobactin-binding periplasmic protein FepB P0AEL6 FEPB_ECOLI Escherichia coli 4 0.7742
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7717
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7673
Mitogen-activated protein kinase 10 P53779 MK10_HUMAN Homo sapiens 5 0.7660
Cytohesin-2 Q99418 CYH2_HUMAN Homo sapiens 4 0.7653
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7648
3',5'-cyclic-AMP phosphodiesterase 4B Q07343 PDE4B_HUMAN Homo sapiens 4 0.7645
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.7639
Cytochrome P450 S6BVH1 S6BVH1_RHOER Rhodococcus erythropolis 3 0.7599
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.7598
NAD(P)H dehydrogenase [quinone] 1 P15559 NQO1_HUMAN Homo sapiens 4 0.7595
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7585
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.7573
Methionine aminopeptidase 2 P50579 MAP2_HUMAN Homo sapiens 3 0.7557
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7531
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7508
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7505
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7497
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.7497
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7495
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7456
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7453
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 4 0.7452
Thymidylate synthase P0A886 TYSY_ECO57 Escherichia coli O157:H7 3 0.7442
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 2 0.7442
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7436
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7408
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 3 0.7402
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7388
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.7383
4-hydroxyphenylacetate 3-monooxygenase Q8YHT7 Q8YHT7_BRUME Brucella melitensis biotype 1 2 0.7374
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7368
UDP-N-acetylmuramoyl-tripeptide--D-alanyl-D-alanine ligase Q8DNV6 Q8DNV6_STRR6 Streptococcus pneumoniae 3 0.7341
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7339
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7338
Vitamin D3 dihydroxylase P18326 CPXE_STRGO Streptomyces griseolus 3 0.7308
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7304
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7275
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7260
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7241
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7222
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7221
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7199
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7197
Cytochrome P450 2C19 P33261 CP2CJ_HUMAN Homo sapiens 3 0.7189
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 4 0.7187
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7183
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7180
Phosphodiesterase Q8WQX9 Q8WQX9_9TRYP Trypanosoma brucei 3 0.7173
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 4 0.7161
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7125
Glutathione S-transferase P P09211 GSTP1_HUMAN Homo sapiens 2 0.7115
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7098
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7091
Methionine aminopeptidase 2 P50579 MAP2_HUMAN Homo sapiens 3 0.7087
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7057
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7012
DNA gyrase subunit A P0AES5 GYRA_SHIFL Shigella flexneri 3 0.7006
4-hydroxyphenylacetate 3-monooxygenase, reductase component Q5SJP7 HPAC_THET8 Thermus thermophilus 3 0.7003

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